Heat, pressure and light-induced interconversion of bisdithiazolyl radicals and dimers

Journal of the American Chemical Society

Volumn 136, Issue 22, 2014, Pages 8050-8062

  Lekin, Kristina ^a   Phan, Hoa ^b   Winter, Stephen M ^a   Wong, Joanne W L ^a   Leitch, Alicea A ^a   Laniel, Dominique ^c   Yong, Wenjun ^d   Secco, Richard A ^d   Tse, John S ^e   Desgreniers, Serge ^c   Dube, Paul A ^f   Shatruk, Michael ^b   Oakley, Richard T ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

^b FLORIDA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF OTTAWA   (Canada)

^d UNIVERSITY OF WESTERN ONTARIO   (Canada)

^e UNIVERSITY OF SASKATCHEWAN   (Canada)

^f MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; DISSOCIATION; MAGNETIC SUSCEPTIBILITY; OPTICAL DATA PROCESSING; SINGLE CRYSTALS; X RAY DIFFRACTION;

ARRHENIUS ACTIVATION ENERGY; CURIE-WEISS BEHAVIORS; EXCITED ELECTRONIC STATE; LINEAR COMPRESSIBILITIES; MAGNETIC SUSCEPTIBILITY MEASUREMENTS; PHOTOCHEMICAL TRANSFORMATIONS; SINGLE CRYSTAL X-RAY DIFFRACTION; VARIABLE TEMPERATURE;

DIMERS;

BISDITHIAZOLYL DIMER; BISDITHIAZOLYL RADICAL; DIMER; RADICAL; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPRESSION; CONDUCTANCE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; ENERGY CONVERSION; ENVIRONMENTAL TEMPERATURE; HEAT; HYDROSTATIC PRESSURE; HYPERBARISM; INTERCONVERSION; LIGHT; MAGNETISM; PHASE TRANSITION; PRESSURE; REACTION ANALYSIS; SOLID STATE; SYNCHROTRON RADIATION; SYNTHESIS; X RAY DIFFRACTION;

EID: 84901947225     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja502753t     Document Type: Article

References (114)

1. Molecular Switches, 2 nd ed.; Feringa, B., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
2. Photoinduced Phase Transitions; Nasu, K., Ed.; World Scientific Publishing: Singapore, 2004.
3. Létard, J.-F.; Guionneau, P.; Goux-Capes, L. Top. Curr. Chem. 2004, 235, 221
4. Bousseksou, A.; Molnár, G.; Salmon, L.; Nicolazzi, W. Chem. Soc. Rev. 2011, 40, 3313
5. Decurtins, S.; Gütlich, P.; Köhler, C. P.; Spiering, H.; Hauser, A. Chem. Phys. Lett. 1984, 105, 1
6. Decurtins, S.; Gütlich, P.; Hasselbach, K. M.; Hauser, A.; Spiering, H. Inorg. Chem. 1985, 24, 2174
7. Sato, O.; Iyoda, T.; Fujishima, A.; Hashimoto, K. Science 1996, 272, 704
8. Hauser, A. Top. Curr. Chem. 2004, 234, 155
9. Sato, O.; Tao, J.; Zhang, Y.-Z. Angew. Chem., Int. Ed. 2007, 46, 2152
10. Spin Crossover in Transition Metal Compounds I-III; Gütlich, P.; Goodwin, H. A., Eds.; Springer: Berlin, Heidelberg, Germany, 2004.
11. Spin Crossover Materials: Properties and Applications; Halcrow, M. A., Ed.; J. Wiley & Sons: Chichester, U.K., 2013.
12. Guionneau, P. Dalton Trans. 2014, 43, 382
13. Ratera, I.; Veciana, J. Chem. Soc. Rev. 2012, 41, 303
14. Nakatsuji, S. Chem. Soc. Rev. 2004, 33, 348
15. Zhu, Z.; Bally, T.; Stracener, L. L.; McMahon, R. J. Am. Chem. Soc. 1999, 121, 2863
16. Sajimon, M. C.; Ramaiah, D.; Suresh, C. H.; Adam, W.; Lewis, F. D.; George, M. V. J. Am. Chem. Soc. 2007, 129, 9439
17. Günaydin-Sen, Ö.; Fosso-Tande, J.; Chen, P.; White, J. L.; Allen, T. L.; Cherian, J.; Tokumoto, T.; Lahti, P. M.; McGill, S.; Harrison, R. J.; Musfeldt, J. S. J. Chem. Phys. 2011, 135, 241101
18. Modarelli, D. A.; Lahti, P. M. J. Am. Chem. Soc. 1991, 113, 6329
19. Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R. G., Ed.; J. Wiley & Sons: Chichester, U.K., 2010.
20. Cordes, A. W.; Haddon, R. C.; Oakley, R. T. Adv. Mater. 1994, 6, 798
21. Oakley, R. T. Can. J. Chem. 1993, 71, 1775
22. Cordes, A. W.; Haddon, R. C.; Oakley, R. T. Phosphorus, Sulfur, Silicon Relat. Elem. 2004, 179, 673
23. Morita, Y.; Suzuki, S.; Sato, K.; Takui, T. Nat. Chem. 2011, 3, 197
24. Haddon, R. C. ChemPhysChem 2012, 13, 3581
25. Rawson, J. M.; Alberola, A.; Whalley, A. J. Mater. Chem. 2006, 16, 2560
26. Awaga, K.; Tanaka, T.; Shirai, T.; Umezono, Y.; Fujita, W. C. R. Chim. 2007, 10, 52
27. Hicks, R. G. Org. Biomol. Chem. 2007, 5, 1321
28. Preuss, K. E. Dalton Trans. 2007, 2357
29. Lahti, P. Adv. Phys. Org. Chem. 2011, 45, 93
30. Boeré, R. T.; Roemmele, T. L. Comp. Inorg. Chem. II 2013, 1, 375
31. Rawson, J. M.; Hayward, J. J. Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium; Devillanova, F.; Du Mont, W.-W., Eds.; Royal Society of Chemistry: Cambridge, U.K., 2013; Vol 2; pp 69-98.
32. Barclay, T. M.; Cordes, A. W.; George, N. A.; Haddon, R. C.; Itkis, M. E.; Mashuta, M. S.; Oakley, R. T.; Patenaude, G. W.; Reed, R. W.; Richardson, J. F.; Zhang, H. J. Am. Chem. Soc. 1998, 120, 352
33. Fujita, W.; Awaga, K. Science 1999, 286, 261
34. McManus, G. D.; Rawson, J. M.; Feeder, N.; van Duijn, J.; McCinnes, E. J. L.; Novoa, J. J.; Burriel, R.; Palacio, F.; Oliete, P. J. Mater. Chem. 2001, 11, 1992
35. Itkis, M. E.; Chi, X.; Cordes, A. W.; Haddon, R. C. Science 2002, 296, 1443
36. Brusso, J. L.; Clements, O. P.; Haddon, R. C.; Itkis, M. E.; Leitch, A. A.; Oakley, R. T.; Reed, R. W.; Richardson, J. F. J. Am. Chem. Soc. 2004, 126, 14692
37. Pal, S. K.; Bag, P.; Sarkar, A.; Chi, X.; Itkis, M. E.; Tham, F. S.; Donnadieu, B.; Haddon, R. C. J. Am. Chem. Soc. 2010, 132, 17258
38. Matsuzaki, H.; Fujita, W.; Awaga, K.; Okamoto, H. Phys. Rev. Lett. 2003, 91, 017403
39. Edkins, R. M.; Probert, M. R.; Robertson, C. M.; Howard, J. A. K.; Beeby, A. RSC Adv. 2014, 4, 5351
40. Miller, J. S. Angew. Chem., Int. Ed. 2003, 42, 27
41. Hicks, R. G. Nat. Chem. 2011, 3, 189
42. Rawson, J. M.; Hayward, J. J. In Spin-Crossover Materials: Properties and Applications; Halcrow, M. A., Ed.; J. Wiley & Sons: Chichester, U.K., 2013; p 235.
43. Lekin, K.; Winter, S. M.; Downie, L. E.; Bao, X.; Tse, J. S.; Desgreniers, S.; Secco, R. A.; Dube, P. A.; Oakley, R. T. J. Am. Chem. Soc. 2010, 132, 16212
44. Nakanishi, W.; Hayashi, S.; Toyota, S. Chem. Commun. 1996, 371
45. Nakanishi, W.; Hayashi, S.; Arai, T. Chem. Commun. 2002, 2416
46. Nakanishi, W.; Hayashi, S.; Morinaka, S.; Sasamori, T.; Tokitoh, N. New J. Chem. 2008, 32, 1881
47. Sharma, S.; Selvakumar, K.; Singh, V. P.; Zade, S. S.; Singh, H. B. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 827
48. Phan, H.; Lekin, K.; Winter, S. M.; Oakley, R. T.; Shatruk, M. J. Am. Chem. Soc. 2013, 135, 15674
49. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. 1969, 8, 781
50. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, Germany, 1970.
51. There are few examples of photochemically driven interconversions involving thiazyl radicals. For example, see Brooks, W. V. F.; Burford, N.; Passmore, J.; Schriver, M. J.; Sutcliffe, L. H. J. Chem. Soc., Chem. Commun. 1987, 69
52. Leitch, A. A.; Yu, X.; Robertson, C. M.; Secco, R. A.; Tse, J. S.; Oakley, R. T. Inorg. Chem. 2009, 48, 9874
53. Bondi, A. J. Phys. Chem. 1964, 68, 441
54. Dance, I. New J. Chem. 2003, 27, 22
55. Eramian, H.; Tian, Y.-H.; Fox, Z.; Beneberu, H. Z.; Kertesz, M. J. Phys. Chem. A 2013, 117, 14184
56. Knop, O.; Boyd, R. J.; Choi, S. J. J. Am. Chem. Soc. 1988, 110, 7299
57. Denk, M. J. Eur. J. Inorg. Chem. 2009, 1358
58. Chen, C. M.; Dojahn, J. G.; Wentworth, W. E. J. Phys. Chem. A 1997, 101, 3088
59. The pressure dependence of the unit cell parameters β- 1b finds a parallel in the behavior of its isostructural selenium-based analog, although the overall compressibility of the latter is smaller, as intermolecular interactions are stronger. See: Lekin, K.; Leitch, A. A.; Tse, J. S.; Bao, X.; Secco, R. A.; Desgreniers, S.; Ohishi, Y.; Oakley, R. T. Cryst. Growth Des. 2012, 12, 4676
60. Cairns, A. B.; Catafesta, J.; Levelut, C.; Rouquette, J.; van der Lee, A.; Peters, L.; Thompson, A. L.; Dmitriev, V.; Haines, J.; Goodwin, A. L. Nat. Mater. 2013, 12, 212
61. Cairns, A. B.; Thompson, A. L.; Tucker, M. G.; Haines, J.; Goodwin, A. L. J. Am. Chem. Soc. 2012, 134, 4454
62. Goodwin, A. L.; Keen, D. A.; Tucker, M. G. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 18708
63. Li, W.; Probert, M. R.; Kosa, M.; Bennett, T. D.; Thirumurugan, A.; Burwood, R. P.; Parinello, R. P.; Howard, J. A. K.; Cheetham, A. K. J. Am. Chem. Soc. 2012, 134, 11940
64. Haines, J.; Chateau, C.; Léger, J. M.; Bogicevic, C.; Hull, S.; Klug, D. D.; Tse, J. S. Phys. Rev. Lett. 2003, 91, 015503
65. Zhou, M.; Wang, K.; Men, Z.; Sun, C.; Li, Z.; Liu, B.; Zou, G.; Zou, B. CrystEngComm 2014, 16, 4084
66. Baughman, R. H.; Galvao, D. S. Nature 1993, 365, 735
67. Baughman, R. H.; Shacklette, J. M.; Zakhidov, A. A.; Stafstrom, S. Nature 1998, 392, 362
68. Baughman, R. H.; Stafstrom, S.; Cui, C. X.; Dantas, S. O. Science 1998, 279, 1522
69. Barnes, D. L.; Miller, W.; Evans, K. E.; Marmier, A. Mech. Mater. 2012, 46, 123
70. Zamir, S.; Bernstein, J.; Greenwood, D. J. Mol. Cryst. Liq. Cryst. 1994, 242, 193
71. Dunitz, J. D.; Bernstein, J. Acc. Chem. Res. 1995, 28, 193
72. Naumov, P.; Sahoo, S. C.; Zakharov, B. A.; Boldyreva, E. V. Angew. Chem., Int. Ed. 2013, 52, 9990
73. Hayes, P. J.; Oakley, R. T.; Cordes, A. W.; Pennington, W. T. J. Am. Chem. Soc. 1985, 107, 1346
74. Oakley, R. T.; Reed, R. W.; Cordes, A. W.; Craig, S. L.; Graham, S. B. J. Am. Chem. Soc. 1987, 109, 7745
75. Boeré, R. T.; Roemmele, T. L.; Yu, X. Inorg. Chem. 2011, 50, 5123
76. Britten, J. F.; Clements, O. P.; Cordes, A. W.; Haddon, R. C.; Oakley, R. T.; Richardson, J. F. Inorg. Chem. 2001, 40, 6820
77. Beer, L.; Cordes, A. W.; Myles, D. J. T.; Oakley, R. T.; Taylor, N. J. CrystEngChem. 2000, 2, 109
78. Parvez, M.; Boeré, R. T. Acta Crystallogr. C 1995, 51, 2118
79. Haynes, D. A. CrystEngComm 2011, 13, 4793
80. Vegas, A.; Pérez-Salazar, A.; Banister, A. J.; Hey, R. G. J. Chem. Soc., Dalton Trans. 1980, 1812
81. Banister, A. J.; Rawson, J. M. Adv. Heterocycl. Chem. 1995, 62, 137
82. Awere, E. G.; Burford, N.; Haddon, R. C.; Parsons, S.; Passmore, J.; Waszczak, J. V.; White, P. S. Inorg. Chem. 1990, 29, 4821
83. Awere, E. G.; Burford, N.; Mailer, C.; Passmore, J.; Schriver, M. J.; White, P. S.; Banister, A. J.; Oberhammer, M.; Sutcliffe, L. H. J. Chem. Soc., Chem. Commun. 1987, 66
84. Alberola, A.; Clements, O. P.; Collis, R. J.; Cubbitt, L.; Grant, C. M.; Less, R. J.; Oakley, R. T.; Rawson, J. M.; Reed, R. W.; Robertson, C. M. Cryst. Growth Des. 2008, 8, 155
85. Bestari, K.; Cordes, A. W.; Oakley, R. T.; Young, K. M. J. Am. Chem. Soc. 1990, 112, 2249
86. Feeder, N.; Less, R. J.; Rawson, J. M.; Oliete, P.; Palacio, F. Chem. Commun. 2000, 2449
87. Beneberu, H. Z.; Tian, Y.-H.; Kertesz, M. Phys. Chem. Chem. Phys. 2012, 14, 10713
88. Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850
89. Mota, F.; Miller, J. S.; Novoa, J. J. J. Am. Chem. Soc. 2009, 131, 7699
90. Clarke, C. S.; Jornet-Somoza, J.; Mota, F.; Novoa, J. J.; Deumal, M. J. Am. Chem. Soc. 2010, 132, 17817
91. Barclay, T. M.; Beer, L.; Cordes, A. W.; Oakley, R. T.; Preuss, K. E.; Taylor, N. J.; Reed, R. W. Chem. Commun. 1999, 531
92. Cozzolino, A. F.; Vargas-Baca, I.; Mansour, S.; Mahmoudkhani, A. H. J. Am. Chem. Soc. 2005, 127, 3184
93. Cozzolino, F.; Vargas-Baca, I. Cryst. Growth Des. 2011, 11, 668
94. Risto, M.; Assoud, A.; Winter, S. M.; Oilunkaniemi, R.; Laitinen, R. S.; Oakley, R. T. Inorg. Chem. 2008, 47, 10100
95. Cornil, J.; Beljonne, D.; Calbert, J.-P.; Brédas, J.-L. Adv. Mater. 2001, 13, 1053
96. Koren, A. B.; Curtis, M. D.; Francis, A. H.; Kampf, J. W. J. Am. Chem. Soc. 2003, 125, 5040
97. Jeftić, J.; Hauser, A. J. Phys. Chem. B 1997, 101, 10262
98. Gütlich, P.; Ksenofontov, V.; Gaspar, A. B. Coord. Chem. Rev. 2005, 249, 1811
99. Létard, J.-F. J. Mater. Chem. 2006, 16, 2550
100. To our knowledge, the highest T observed for a LIESST state is 180 K. See: Li, D.; Clérac, R.; Roubeau, O.; Harté, E.; Mathoniére, C.; Le Bris, R.; Holmes, S. M. J. Am. Chem. Soc. 2008, 130, 252
101. SAINT, version 6.22; Bruker Advanced X-ray Solutions, Inc.: Madison, WI, 2001.
102. Sheldrick, G. M. Acta Crystallogr. A 1990, 46, 467.
103. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Gottingen: Gottingen, Germany, 1997.
104. SHELXTL, Program Library for Structure Solution and Molecular Graphics, version 6.12; Bruker Advanced X-ray Solutions, Inc.: Madison, WI, 2001.
105. Smith, J. S.; Desgreniers, S. J. Synchrotron Radiat. 2009, 16, 83
106. Boultif, A.; Louer, D. J. Appl. Crystallogr. 2004, 37, 724
107. David, W. I. F.; Shankland, K.; van de Streek, J.; Pidcock, E.; Motherwell, W. D. S.; Cole, J. C. J. Appl. Crystallogr. 2006, 39, 910
108. Rietveld, H. M. J. Appl. Crystallogr. 1969, 2, 65
109. Larson, A. C.; Von Dreele, R. B. General Structure Analysis System (GSAS); Report LAUR Los Alamos National Laboratory: Los Alamos, NM, 2000; pp 86-748.
110. Secco, R. A. Can. J. Phys. 1995, 73, 287
111. Secco, R. A.; Schloessin, H. H. J. Appl. Phys. 1986, 60, 1625
112. Carlin, R. L. Magnetochemistry; Springer-Verlag, New York, 1986.
113. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. W.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
114. Neese, F. Wiley Interdiscip. Rev. Comput. Mol. Sci. 2012, 2, 73